1,2-Dichloroethane → HCID 67441507, compound

HRID 1664206Notes

Reaction equation

HRID 1664206 reaction equation
CO[C:3](=[O:50])[C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C@H:24]([NH:42]C(OC(C)(C)C)=O)[C@H:25]([OH:41])[CH2:26][NH:27][C:28]3([C:31]4[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=[CH:33][N:32]=4)[CH2:30][CH2:29]3)[CH:18]=2)[CH:5]=1.[OH-].[Na+].Cl.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>O>[C:37]([C:35]1[CH:34]=[CH:33][N:32]=[C:31]([C:28]2([NH:27][CH2:26][C@H:25]([C@@H:24]3[CH2:23][C:19]4[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=4)[O:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:6]4[CH:5]=[C:4]([CH:9]=[C:8]([CH3:10])[N:7]=4)[C:3](=[O:50])[NH:42]3)[OH:41])[CH2:29][CH2:30]2)[CH:36]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67440569HCID 67440569, compound

Product 1

HCID 67441507HCID 67441507, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 60 mg (0.0868 mmol) 2-[4-(3-{(2S,3R)-2-tert-butoxycarbonylamino-4-[1-(4-tert-butyl-pyridin-2-yl)-cyclopropylamino]-3-hydroxy-butyl}-phenoxy)-butoxy]-6-methyl-isonicotinic acid methyl ester is treated with 0.17 ml 1N aq sodium hydroxide and stirred for 18 h. The mixture is acidified with 0.17 ml 1N aq hydrochloric acid and evaporated. The residue is taken up into 3 ml 4N hydrochloric acid in dioxan, stirred for 2 h and evaporated. The product is taken up in 20 ml DCM. To the stirred mixture at +4° C. is added subsequently 22.3 mg (0.13 mmol) HOBt, 25 mg (1.5 mmol) EDC and 0.048 ml N-methylmorpholine. The mixture is slowly warmed to rt and stirred 18 h. Water is added and the organic phase is washed with 5% aq sodium bicarbonate and brine, dried over sodium sulfate and chromatographed on silica gel using a gradient of DCM and MeOH/25% aq NH3 2-10%. The title compound is obtained as a colorless resin.

Workup

  1. customevaporated
  2. stirringstirred for 2 h
  3. customevaporated
  4. stirringstirred 18 h
  5. washthe organic phase is washed with 5% aq sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. customchromatographed on silica gel using a gradient of DCM and MeOH/25% aq NH3 2-10%

Sources & evidence

ORD record
ord-ef21ca8923ae4f3d85bc3c9a3c98144b
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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